Freelance job security
"and if that job had a chance to be more permanent, would have taken it."
Should have stayed contracting, best decision I ever made. I've had more job security since going freelance than I ever did as a permie, since it's all an illusion anyway. At least being freelance you know what the risks are and can mitigate them (which you typically do with a high day rate and only pay yourself a reasonable salary/dividend - that way your company always has money in it to pay you if you are between contracts).
You also know to have 6 months living costs in the bank, just in case.
All that extra money from being a contractor shouldn't really be used to fuel a rock-star lifestyle (unless you want it to end like one too) - it should be used to purchase safety nets.
The upshot of contracting is that you typically end up working on new projects (fixed budget/timelines) and often get to play with new toys and keep your skills up for free, which in turn makes you more employable which provides you with a solid reputation upon which to raise your rates.
Biting the hand that feeds IT
